ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A new unnatural macrocyclic trichothecene, an analogue of verrucarine A (1), which was named 3-Isoverrucarin A ((1″-O)(3→4)abeo-verrucarin A; 3) was synthesized starting from anguidine (5). The two key reactions were the removal of the 4β-acetoxy group of anguidine (5) by a Barton deoxygenation and the final macrolactonization. During the cyclization procedure, two unexpected new macrocyclic by-products, which were named verrucinol (19) and verrucene (20), were formed. They represent novel types of macrocyclic trichothecenes, the macrolidic moiety of verrucene (20) consisting only of the (Z,E)-muconic-acid residue. The formation of the analogous macrolide 26 of verrucene (20) was not possible, probably because the ring strain is too strong.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19880710808
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